4-AMINO-2-QUINOLINONE DERIVATIVES

Abstract: The present invention relates to novel 4-amino-2-quinolinone derivatives of formula (I) useful as fungicides, insecticides and herbicides. In said formula, R1, R2, R3 and R4 are independently hydrogen, halogen, C1-C10 alkyl, C1-C3 haloalkyl, C1-C8 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 haloalkylthio, NO2, CN, C1-C4 alkoxy carbonyl, phenyl, phenoxy, benzoyl, benzenesulfonyl, benzyl or morpholine; R5 is C1-C6 alkyl, cyclopropyl, phenyl, halophenyl, benzyl or phenylthiomethyl; R6 is selected form hydrogen, C1-C5 alkyl, C3-C6 alkenyl and C3-C6 alkynyl group; R7 is (a), (b), (c), (d), (e), (f), (g), (h), (i); wherein, R8, R9, R10, R11, R12, R13, R14, R15, R16 is hydrogen, halogen, C1-C6 alkyl, alkoxyalkyl, halophenyl, phenyl or (R20)3Si and R8, R9, R10 are not hydrogen at same time; R17 is hydrogen or C1-C5 alkyl; R18, R19 is C1-C5 alkyl; X is oxygene or sulfur; Y is sulfur or -S(=O)-; R20 is C1-C5 alkyl; m, n, p, q, is 0 to 4.

Description: 4-AMINO-2-QUINOLINONE DERIVATIVES BACKGROUND OF THE INVENTION Field of the Invention The present invention relates to novel 4-amino-2-quinolinone derivatives of the following formula(I) useful as fungicides, insecticides and herbicides. R! H wherein, R j , R 2 , R 3 and R 4 are independently hydrogen, halogen, C .-C 10 alkyl, C j - haloalkyl, C r alkoxy, C,-C 3 haloalkoxy, C ,-C 3 alkylthio, C ,-C j haloalkylthio, NO 2 , CN, C j - alkoxy carbonyl, phenyl, phenoxy, benzoyl, benzenesulfonyl, benzyl or morpholine ; R 5 is C r C 6 alkyl, cyclopropyl, phenyl, halophenyl, benzyl or phenylthiomethyl ; R 6 is selected from hydrogen, C r C 5 alkyl, C 3 -C 6 alkenyl and C 3 -C 6 alkynyl group; R 7 is Rl7 Rl7 N (CH 2 )p-γ— R 19 , — CH 2 CN , - CH 2 .^^ wherein, R 8 , R 9 , R 10 , R n , R 12 , R 13 , R ]4 , R 15 , R 16 is hydrogen, halogen, C,-C 6 alkyl, alkoxyalkyl, halophenyl, phenyl or (R-^Si and R 8 , R 9 , R ]0 are not hydrogen at the same time ; R 17 is hydrogen or C,-C 5 alkyl ; R j g, R 19 is C.-C 5 alkyl ; X is oxygen or sulfur ; Y is sulfur or -S(=O)- ; R 20 is C,-C 5 alkyl ; m, n, p, q is 0 to 4. Description of the Related Art Prior to this invention, one report on the synthesis of 3-acetyl-4-dimethylamino- 2-quinolinone from phenylisocynate and l-dimethylamino-3-oxo-l-butylene by [4+2] cycloaddition reaction (Helv. Chim. Acta., 1969, 52, 2641.) was disclosed but no attempt for the evaluation of biological activity of the related compounds was reported. According to the known methods, it is difficult to introduce various substituents to aromatic ring, 4-amino group, and 3-acyl group of 2-quinolinone skeleton. Especially, synthesis of 4-monosubstituted amino-2-quinolinones which are core of the present invention is impossible to be produced by known methods. In the present invention, varietiy of new 4-amino-2-qui noli none derivatives having various substituents were synthesized conveniently from various amines and 4- sulfinyl-2-quinolinones of which synthesis was previously disclosed by present inventors(Korea Patent No.70672). Moreover new 4-amino-2-quinolinone derivatives of the present invention showed powerful fungicidal activity as well as insecticidal and herbicidal activity. Therefore, the present invention contains development of novel 4-amino-2- quinolinone derivatives that have superior fungicide, insecticide and herbicide activities and their preparation for use. SUMMARY OF THE INVENTION The objective of the present invention is to provide novel 4-amino-2-quinolinone derivatives of formula(I) which have fungicidal, insecticidal and herbicidal activity and their preparation processes. Another objective is to provide agricultural preparation containing a compound of formula(I) as active ingredient. DETAILED DESCRIPTION OF THE INVENTION The present invention relates to 4-amino-2-quinolinone compounds of the formula(I) and agricultural preparations containing compounds of the formula(I) as active ingredient. wherein, R„ R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are respectively defined as described previously. In this invention, 4-amino-2-quinolinone compounds of the formula(I) were prepared by reacting 4-sulfϊnyl-2-quinolinone of for ula(II) with the amines(HNR 6 R 7 ) of the formula(III) in presence of inert solvent. ( ll ) ( l ) wherein, R., R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are defined as previously and R 21 is C,-C 3 alkyl. When the amine compound of formula(III) is in salt form, such as primary or secondary ammonium hydrochlorides(HNR 6 R 7 -HCl), sulfates , carbonates, oxalates or tosylates, 1 ~ 2 equivalents of an acid remover, for example, trialkylamines (such as triethylamine) or inorganic base (such as sodium hydroxide, potassium carbonate), may be used . The inert solvents used in the present invention may be, for example, ethers such as diethylether, diisopropyl ether, tetrahydrofuran, dioxane, diphenylether, etc. ; hydrocarbons such as benzene, toluene, xylene, ligroine, etc. ; hydrocarbon halides such as dichloroe thane, chloroform, carbon tetrachloride, etc. ; esters such as ethyl acetate, ethyl propionate, etc. ; chloro benzenes such as monochlorobenzene, dichloro benzene, etc. ; aprotic polar solvents such as N,N-dimethylformamide, dimethyl sulfoxide, etc.. The above reaction can be carried out in the absence of solvent but for effective reaction use of proper solvent is recommended and pyridine and trialkylamine may be used for two purposes of base or a solvent. The reaction can be carried out at 0 ~ 260°C, preferably between room temperature and boling point of the solvent, and then the reaction time is preferably of 0.5-8 hr. As a result of the reaction, when the free amine compound(HNR 6 R 7 ) of formula(III) is used, the crude product is obtained by evaporating the solvent under the reduced pressure. But, when the salt form of amine compound of formula(III) is used, the crude product may be obtained by following process ; the solvent is evaporated under the reduced pressure ; water is added to dissolve the salts ; the resulting mixture is extracted with water-immiscible organic solvents such as methylenεchloride, chloroform, ethyl acetate, etc. ; and the organic layer is evaporated under the reduced pressure to afford the crude product. Compounds (lb) shown below can be obtained by acid hydrolysis of compounds (la), a kind of 4-amino-2-quinolinone derivatives of formula(I) ( la ) ( lb ) wherein, R 1? R 2 , R 3 , R 4 , R 5 , R 6 and R 18 are defined as previously. The hydrolysis reaction of compounds (la) to compounds (lb) can be done in the presence of mineral acids such as hydrochloric acid, sulfuric acid, etc. or organic acids such as acetic acid, propionic acid, etc. and the reaction could be carried from room temperature to the boiling point of the solvent. The 4-amino-2-quinolinone _ ..rivatives of formula(I) described above may be purified by column chromatography or recrystallized from the following solvents ; alcohol solvents such as methanol, ethanol, etc. ; esters of organic acid such as ethyl acetate, methyl acetate, etc. ; hydrocarbon solvents such as pentane, hexane, etc. ; ethers such as ethylether, tetrahydrofuran, etc. New compounds of 4-amino-2-quinolinone(I) prepared by present invention are typically listed in following Table (I). Table 1. 4-Amino-2-quinolinone derivatives R5 ( I ) Ri H No. R, R 2 R. R_ R5 R 7 m.p.(°C) H,C- H 2 C- CF, H H H Me 36-38 H,C- H 2 C- Cl Cl H H Me 48-50 H ? C- H 2 C- 7 CF 3 H Cl H c-Pr 104-107 H 9 C- H 2 C- 8 CF 3 H Cl H i-Pr 83-85 .OMe H 2 C-< 9 CF 3 H Cl H c-Pr H OMe 191-193 .OMe H 2 C— 10 CF 3 H Cl H i-Pr H 1 OMe 159-161 1 OMe H 2 C-< 15 11 CF 3 H Cl H Et H OMe 171-172 12 CF 3 H Cl H Me Me H C- 86-87 13 CF 3 H Cl H i-Pr Me H 2 C — 99 _ 101 No. R, R j R 3 R 4 R j Re R. m.p.(°C) 14 CF 3 H Cl H c-Pr Me H ? C- 118-120 15 CF 3 H H H Me Me H 2 C-= 64-69 5 16 CF 3 H Cl H Et Me H?C-≡ 70-72 17 Cl Cl H H Me Me H?C-≡ 110-112 .OMe H 2 C-< 18 Cl Cl H H Me H OMe 210-211 OMe H 2 C-< 19 CF 3 F H H Me H OMe 161-162 OMe H 2 C— < 20 Cl H H NO 2 Me H OMe 213-214 ιo 21 CF 3 H Cl H c-Pr H 179-181 22 CF 3 H Cl H Et H H 2 C-≡ 185-186 23 H H n-C 6 H 13 H Me H H 2 C-≡ 129-132 24 CF 3 H Cl H Me H H 2 C-≡ 210-212 25 Me H H H Me H H ? C-≡ 232-234 15 26 Cl H H NO 2 H H 217-219 27 Cl Cl H H Me H 245-249 28 CF 3 H Cl H i-Pr H H,C-≡ 166-168 29 CF 3 H Cl H Me H H 2 C— -≡ 213-215 30 CF 3 H Cl H i-Pr H H 2 C-≡ 167-169 20 o 32 CF 3 H Cl H i-Pr H "^ H 53.54 33 CF 3 H Cl H i-Pr H -^- " ^Cl E & z 34 CF 3 H Cl H i-Pr H H 2 C-=- SiMe 3 \ηη_\η% 35 CF 3 H Cl H c-Pr H H 2 C-= 183-184 36 CF, H Cl H Me H 37 CF 3 H Cl H i-Pr H 38 CF 3 H Cl H i-Pr H 39 CF 3 H Cl H Me H 40 CF 3 H Cl H c-Pr H H 2 C-=≡- SiMe 2 Bu-t 191 . 193 41 CF 3 H Cl H c-Pr H H 2 C-≡- SiMe 3 181 . 182 42 CF 3 H Cl H Me H H 2 C-≡- SiMe 3 172 _173 43 CF, H Cl H Me H H 2 C- i ≡- SiMe 2 Bu-t 191 . 192 44 CF H Cl H Et H H2C — 183-184 H C^ 0B 45 CF 3 H Cl H Me H 2 OEt 104-105 46 CF 3 H Cl H Me H H 2 C^= 132-133 47 CF 3 H Cl H Me H H 2 c-=— 240-241 No. F. R j R 3 R 4 R S Rg R, m.p.(°C) 48 Cl , H Cl H i-Pr H H 2 C-=- SiMe 2 Bu-t 185 . 186 49 CF, H Cl H Et H H 2 C-^=^ SiMe 3 154 . 15 5 50 CF, H Cl H Et H H 2 C-=- SiMe 2 Bu-t 153 . 154 Me I c— 1 51 CF 3 H Cl H Me H Me 172-173 52 CF, H Cl H Me H " '*^ ^ HH 115566--1157 53 CF 3 H Cl H Et H H 2 C^---— 183-184 54 CF 3 H Cl H Et H H 2 C— = 124-126 55 CF 3 H Cl H Et H H2 188-189 56 CF 3 H Cl H c-Pr H H 2 C-=— 196-197 57 CF, H Cl H c-Pr H H 2 C— ≡ 134-135 58 CF 3 H Cl H c-Pr H Hz ° °x2 181-182 OEt 59 CF 3 H Cl H c-Pr H H2C — L OEt 111-112 60 CF, H Cl H Et H 61 CF 3 H Cl H c-Pr H 62 CF 3 H Cl H Me H 63 CF 3 H Cl H c-Pr H 64 CF 3 H Cl H Et H NO. R j Ra R. R 4 Rs R. R 7 m.p.(°C) O 65 CF, H Cl H Et H H 2 C-**»--»--** **** -* ' H 3 91-94 o 66 CF 3, H Cl H c-Pr H H 2 C- * ^J *« . H 127-130 r CI 5 67 CF 3 H Cl H Me H H C" ^ E&Z 68 CF 3 H Cl H Et H H2C E&Z 69 -CHCH=CHCH- Cl H c-Pr H H 2 c-≡ 222(dec.) 70 CF 3 H H H Me H H 2 C-≡ 192-194 71 Cl H H H Et H H 2 C-≡ 212-214 10 72 CF 3 H Cl H c-Pr H H2c_ «s. 136-137 73 CF 3 H Cl H c-Pr H 2C-≡ H 2 C-≡ 140-142 74 CF 3 H Cl H i-Bu H H 2 C-≡≡ 179-180 75 CF 3 H Cl H Me H H2 C-^ 136-137 76 CF 3 H Cl H Et H H2C" ^ 149-150 15 77 CF 3 H Cl H i-Pr H 2 ^ 135-136 78 CF 3 H Cl H c-Pr H H2C E & Z 79 H H Cl H Me H H 2 C-≡ 166-168 80 F H H H H H H 2 C-≡ 206-208 81 Me H H H Me H H 2 c-≡ 229-231 20 No. R j R J R 3 R 4 R j > R , m.p.(°C) 82 CF 3 H Cl H c-Pr H H 2 C-=-Ph 2 27-228 83 σ- 3 H Cl H Et H H 2 C-=-Ph 191.193 84 CF 3 H Cl H i-Pr H H 2 C-≡-Ph 166-167 85 CF 3 H Cl H Et H 2 C-_≡ H 2 C-≡ 91 _ 94 86 CF 3 H Cl H Me H 2C-≡ H 2 C-≡ 115-117 87 CF 3 H Cl H i-Pr H H 2 C-≡ 88 H -OCH 2 CH 2 O- H c-Pr H H 2 C-= 230(dec.) OEt 89 CF 3 H Cl H i-Pr H HaC^- Q Et 113-114 O o 90 CF 3 H Cl H i-Pr H 154-155 91 CF, H Cl H i-Pr H H ? C-≡- 196-197 92 CF, H Cl H i-Bu H H 2 c-~-= 128-130 93 CF 3 H Cl H i-Pr H2C" 93-94 94 CF, H H H Me " H 2 2 'C--≡ H 2 c-= 94 . 95 H 2 C > ^_ 95 CF, 3 H Cl H Et H ~ ^ O Q . r 159-161 96 CF 3 H Cl H i-Bu H 174-175 H r 1 J 97 CF 3 H Cl H i-Pr H " 2 ^ ^ 0 140-142 o"S H Γ JL J 98 CF, H Cl H c-Pr H " Z ^ N ^O' 166-168 NO. R j R J R, R, Rs Re R. m.p.(°C) 99 CF, H Cl H Me H H 2 C-≡- Ph 200-201 H ? C * "— __— *»• 100 CF, H Cl H c-Pr H OMe 5 101 CF, H Cl H PhCH, H H ? C-= 154-156 H 2 C ^ SMe 102 CF, H Cl H Me H 146-147 . ■ ≡- Ph 103 CF, H Cl H Me H H,C 125-127 104 CF, H Cl H i-Bu H HpC r≡-Ph 100-102 j≡- Ph 105 CF, H Cl H c-Pr H H 2 C 122-126 -^ϊ jj j≡- Ph 10 106 CF, H Cl H Et H H 2 C 107-109 II 107 CF, H Cl H c-Pr H H 2 C- - Ph-p-F 185-186 108 CF, H Cl H i-Bu H H 2 C-^- Ph-p-F 121-123 109 CF, H Cl H Et H HaC-^ Ph-p-F 164-166 15 1 11 CF, H Cl H i-Pr H 222-224 M-.V 112 Cl H H H Et H 238-239 H?C- 113 CF, H Cl H Et H ' OMe 141-143 C . 114 CF, H Cl H Me H H 2 C_-_^ϋ_ Ph-p-F 147 . 14 9 115 CF, H Cl H i-Pr H H 2 C-*~ Ph-p-F 100-102 No. R, R j R 3 R 4 R 5 Re R. m.p.(°C) p 116 CF, H Cl H i-Pr H 144-145 S 5--V H 2 C« -< _» ' *- ς ' 118 CF 3 H Cl H Me H " 2 ^ s 107-110 120 CF 3 H Cl H c-Pr H H 2 C_^ S 135.137 S- H 2 C^Λ„ 121 CF 3 H Cl H i-Bu H ^ ^ ' S 92-94 122 H H F H Me H H 2 C^^N 307 . 309 123 CF, 3 H Cl H Et H 243-244 c* 124 CF, H Cl H c-Pr H H2C Et 152-153 "' 11 125 CF 3 H Cl H Me H H C Et 135-136 126 CF 3 H Cl H Me H H * C "^ 109-111 127 CF 3 H Cl H Et H Hz ° = 117-118 128 CF 3 H Cl H c-Pr H H2 °" = 139-141 129 CF 3 H Cl H i-Bu H H2 ° ~ 94-95 130 CF 3 H Cl H Me H H2 C _ , N 2 32-234 N-r. 131 CF 3 H Cl H i-Bu H 2 C-_ , N 179.131 Preparation of the present compounds of formula (I) is illustrated further in the following examples. EXAMPLE 1 : 6-Chloro-3-cyclopropanecarbonyl-4-(2,2-dimethoxyethylamino)- 5 8-trifluoromethyl-2-quinolinone(9). 6-Chloro-3-cyclopropanecarbonyl-4-methylsulfoxy-8-trifluormethyl-2- quinolinone(377mg,lmmol) and 2,2-dimethoxyethylamine(105mg,lmmol) were dissolved in tetrahydrofurane(20ml) and stirred for 24hr at room temperature. After completion of reaction, solvent was removed under reduced pressure and residue was o recrystallized from ethanol to give desired product(335mg, yield : 80%). Η-NMR(CDC1 3 ) : δ 0.7-1.2(m,4H), 3.4(s, 6H), 3.6-3.8(m,lH), 4.4(t, 1H), 4.5-4.9(m, 2H), 7.7(d,lH), 8.8(d, 1H), 9.5(br, 1H), 11.6(br, 1H). EXAMPLE 2 : 6-Chloro-4-(2,2-dimethoxyethyl amino)-3-isobutyryl-8- 5 trifluoromethyl-2-quinolinone(10). 6-Chloro-3-isobutyryl-4-methylsulfoxy-8-trifluoromethyl-2-quinolinone(379mg, lmmol) and 2,2-dimethoxyethylamine(105mg, lmmol) were used and the reaction was carried out as in the above process of example 1 to obtain the desired product (307mg, yield : 73%). 0 Η NMR (CDC1 3 ) : δ 1.5(d, 6H), 3.6-3.8(m, 1H), 3.8(s, 6H), 4.4(t, 1H), 4.5-4.9(m, 2H), 8.1(d, 1H), 8.8(d, 1H), 9.9(br, 1H), 12.2(br, 1H). EXAMPLE 3 : 3-Acetyl-6-chloro-4-(N-methyl-N'-propargylam ino)-8- trifluoromethyl-2-quinolinone(12) 5 3-Acetyl-6-chloro-4-methylsulfoxy-8-trifluoromethyl-2-quinolinone(351mg, lmmol) and N-methyl-N'-propargylamine(69mg, lmmol) were used and the reaction was carried out as in the above process of example 1 to obtain the desired product (235mg, yield : 66%). Η NMR (CDC1 3 ) : δ 2.6(t, 1H), 3.0(s, 3H), 3.4(s, 3H), 4.6(d, 2H), 8.2(d, 1H), 8.6(d, 1H), 14.0(br, 1H). EXAMPLE 4 : 3-Acetyl-4-(N-methyl-N'-propargylamino)-8-trifluoromethyl-2- quinolinone(15). 3-Acetyl-4-methylsulfoxy-8-trifluoromethyl-2-quinolinone(317mg, lmmol) and N-methyl-N'-propargylamine(69mg, lmmol) were used and the reaction was carried out as in the above process of example 1 to obtain the desired product (210mg, yield : 65%). Η NMR (CDC1 3 ) : δ 2.5(t, 1H), 2.9(s, 3H), 3.3(s, 3H), 4.5(d, 2H), 7.4(t, 1H), 8.2(d, 1H), 8.5(d, 1H), 9.6(br, 1H). EXAMPLE 5 : 6-Chloro-3-cyclopropanecarbonyl-4-propargylamino-8- trifluormethyl-2-quinolinone(21 ). 6-Chloro-3-cyclopropanecarbonyl-4-methylsulfoxy-8-trifluormethyl-2- quinolinone(377mg, lmmol) and propargylamine(55mg, lmmol) were used and the reaction was carried out as in the above process of example 1 to obtain the desired product (265mg, yield : 72%). Η NMR (CDC1 3 ) : δ 1.3-1.6(m, 4H), 2.9(t, 1H), 3.9-4.3(m, 1H), 4.6(q, 2H), 8.2(d, 1H), 8.8(d, 2H), 12.4(br, 1H). EXAMPLE 6 : 3-Acetyl-6-chloro-4-propargylamino-8-trifluoromethyl-2- quinolinone(24). 3-Acetyl-6-chloro-4-methylsulfoxy-8-trifluoromethyl-2-quinolinone(351mg, lmmol) and propargylamine(55mg, lmmol) were used and the reaction was carried out as in the above process of example 1 to obtain the desired product (284τ $ϋ, yield : 83%). 'H NMR (CDC1 3 ) : δ 2.9(t, 1H), 3.0(s, 3H), 4.5(q, 2H), 8.0(d, 1H), 8.8(d, 2H), 12.3(br, 1H). EXAMPLE 7 : 6-Chloro-4-(3,3-diethoxypropylami no)-3-isobutyryl-8- trifluoromethyl-2-quinolinone(31 ). 6- Ch loro -3 - i sobu tyryl -4 -m eth yl s ulfo xy -- 8 -tri flu oromethy l-2- quinolinone(379mg, lmmol) and 3,3-diethoxypropylamine(147 g, lmmol) were used and the reaction was carried out as in the above process of example 1 to obtain the desired product (335mg, yield : 78%). Η NMR(CDC1 3 ) : δ 0.7-1.5(m, 12H), 2.0-2.4(m, 2H),3.2-4.0(m, 6H), 4.2(m, 1H), 4.7(t, lH), 7.8(d, 1H), 8.0(br, 1H), 11.9(br, 1H). EXAMPLE 8 : 6-Chloro-3-isobutyryl-4-(3-oxopropylamino)-8-trifluoromethyl- 2-quinolinone(32). 6-Chloro-4-(3,3-diethoxypropylamino)-3-isobutyryl-8-trifluoromethyl-2- quinolinone(31) was dissolved in 80% aqueous acetic acid(20ml) and stirred for 2h at 70°C. After cooling to room temperature, water(20ml)was added and the mixture was extracted with ethyl acetate(30ml). Organic layer was dried(MgSO 4 ), filtered, evaporated and purifed by silicagel chromatograph(n-Hexane and Ethyl acetate) to give desired product(280mg, yield : 72%). Η NMR(CDC1 3 ) : δ 1.3(d, 6H), 3.1(t, 2H), 3.7(q, 2H), 4.2(m, 1H), 7.8(d, 1H), 8.5(d, lH), 9.1(br, 1H), 10.0(s, 1H), 11.2(br, 1H). EXAMPLE 9 : 3-Acetyl-6-chloro-8-trifluoromethyl-4-(3-trimethylsilyl- propargyl-amino)-2-quinolinone(42). 3-Acetyl-6-chloro-4-methylsulfoxy-8-trifluoromethyl-2-quinolinone(351mg, lmmol), 3-trimethylsilylpropargylamine hydrochloride(164mg, lmmol) and excess triethylamine in tetrahydrofurane(20ml) were stirred for 24h at room temperature. After evaporating the solvent, 20ml of methylene chloride was added and the mixture was washed with water(20ml). Drying(MgSO 4 ) and removing the solvent under reduced pressure gave crude product. Re crystallization in ethanol gave pure product(330mg, yield : 80%). Η NMR (CDC1 3 ) : δ 0.2(s, 9H), 2.7(s,3H), 4.3(d,2H), 7.8(d,lH), 8.5(br, 1H), 8.6(d, 1H), 12.0(br, 1H). EXAMPLE 10 : 6-Chloro-4-propargylamino-3-propionyl-8-trifluoromethyl-2- quinolinone(44). 6-Chloro-4-methylsulfoxy-3-propionyl-8-trifluoromethyl-2-quinolinone(365mg, lmmol) and propargylamine(55mg, lmmol) were used and the reaction was carried out as in the above process of example 1 to obtain the desired product (310mg, yield : 87%). Η NM T DC1 3 ) : δ 1.2(t, 3H), 2.7(t, 1H), 3.4(q, 2H), 4.3(d, 2H), 7.9(d, 1H), 8.6(br, 1H), 8.7 (d, 1H), 12.2(br, 1H). EXAMPL_ 11 : 3-Acetyl-6-c hloro-4-( l , l -dim ethylpropargylamino)-8- trifluoromethyl-2-quinolinone(51 ). 3-Acetyl-6-chloro-4-methylsulfoxy-8-trifluoromethyl-2-quinolinone(351mg, lmmol) and l,l-dimethylpropargylamine(83mg, lmmol) were used and the reaction was carried out as in the above process of example 1 to obtain the desired product (322mg, yield : 87%). Η NMR (CDC1 3 ) : δ 1.5(s, 6H), 2.5(t, 1H), 2.6(s, 3H), 7.7(m, 1H), 8.4(m, 1H), 9.1(br, 1H), 12.0(br, 1H). EXAMPLE 12 : 3-Acetyl-6-chloro-4-(3-phenylallylamino)-8-trifluoromethyl-2- quinolinone(62). 3-Acetyl-6-chloro-4-methylsulfoxy-8-trifluoromethyl-2-quinolinone(351mg, lmmol) and 3-ρ πylallylamine(83mg, lmmol) were used and the reaction was carried out as in the above process of example 1 to obtain the desired product (286mg, yield : 68%). Η NMR (CDC1 3 ) : δ 2.8(s,3H), 4.3(t, 2H), 6.0-6.7(m, 2H), 7.4(s, 5H), 7.7(d, 1H), 8.1(br, 1H), 8.5(d, 1H), 12.1(br, 1H). EXAMPLE 13 : 6-Chloro-4-(2-chloroallylamino)-3-propionyl-8-trifluoromethyl- 2-quinolinone(76). 6-Chloro-4-methylsulfoxy-3-propionyl-8-trifluoromethyl-2-quinolinone(365mg, lmmol) and 2-chloiOallylamine(92mg, lmmol) were used and the reaction was carried 5 out as in the above process of example 1 to obtain the desired product (279mg, yield : 71%). Η NMR (CDCy : δ 1.2(t, 3H), 3.3(q, 2H), 4.2(d, 2H), 5.6(s, 2H), 7.8(d, 1H), 8.0(br, 1H), 8.5(d, 1H), 12.3(br, 1H). 10 EXAMPLE 14 : 6-Chloro-4- (N,N'-dipropargyl am ino)-3-isobutyryl-8- trifluoromethyl-2-quinolinone(93). 6-Chloro-3-isobutyryl-4-methylsulfoxy-8-trifluoromethyl-2-quinolinone(379mg, lmmol) and N,N'-dipropargylamine(93mg, lmmol) were used and the reaction was carried out as in the above process of example 1 to obtain the desired product (290mg, 15 yield : 71%). Η NMR(CDC1 3 ) : δ 1.2(d, 6H), 2.3(t, 2H), 4.0-4.3(m, 1H), 4.3(d, 4H), 8.0(d, 1H), 8.3(d, 1H), 13.1 (br, 1H). EXAMPLE 15 : 3-A cety l- 6- chl oro -4 -( 3- ph en yl p ro pargy lam ino )- 8- 20 trifluoromethyl-2-quinolinone(99). 3-Acetyl-6-chloro-4-methylsulfoxy-8-trifluoromethyl-2-quinolinone(351mg, lmmol) and 3-phenylpropargyl amine hydrochloride(167mg, lmmol) were used and the reaction was carried out as in the above process of example 10 to obtain the desired product (305mg, yield : 73%). 25 Η NMR (CDC1 3 ) : δ 2.7(s, 3H), 4.5(d, 2H), 7.5(s, 5H), 7.8(d, 1H), 8.6(d, 2H), 12.0(br, 1H). EXAMPLE 16 : 3-Acetyl-6-chloro-4-methylthioethylamino-8-trifluoromethyl-2- quinolinone(102). 3-Acetyl-6-chloro-4-methylsulfoxy-8-trifluoromethyl-2-quinolinone(351mg, lmmol) and methylthioethylamine(91mg, lmmol) were used and the reaction was carried out as in the above process of example 1 to obtain the desired product (287mg, yield : 76%). Η NMR (CDCy : δ 2.15(s, 3H), 2.7(s, 3H), 2.8(t, 2H), 3.6(q, 2H), 7.7(br, 1H), 8.1(br, 1H), 8.5(br, 1H), 12.0(br, 1H). EXAMPLE 17 : 3-Acetyl-6-chloro-4-[2-(4-fluorophenyl)-2,3-butadienylamino]- 8-trifluoromethyl-2-quinolinone(114). 3-Acetyl-6-chloro-4-methylsulfoxy-8-trifluoromethyl-2-quinolinone(351mg, lmmol) and methylthioethylamine(91mg, lmmol) were used and the reaction was carried out as in the above process of example 1 to obtain the desired product (369mg, yield : 82%). -B NMR (CDC1 3 ) : δ 2.6(s, 3H), 3.6(t,2H), 5.2(t, 2H), 7.2(m, 4H), 7.8(d, 1H), 8.5(br, 1H), 8.6(d, 1H), 11.8(br, 1H). The compounds of formula(I) according to the present invention have highly curative and protective fungicidal activity for plant phathogens as follows ; for example, rice blast(ftπ ' c_//aπ ' a oryzae), rice sheath bligh t(Rhizoctonia solanf), cucumber gray mold( Botrytis cinerea), cucumber powdery mildew( Sphaerotheca fuliginea), cucumber downy mildew( Pseudoperonospora cυbensis), grape downy mildew(P/as/j.qpora viticola), tomato late blight(PΛ topΛtΛora infestans), rice brown spot(Cochliobolus miyabeanus), peanut brown leaf spot( Cercospora arachidicola), barley powdery mildew(fijsipΛe graminis), wheat leaf rust( Puccinia recondita), wheat stem rust(Puccznis graminis), and wheat eye spot(Pseudocercosporella heφotrichoides). Especially, the compounds of present invention showed strong fungicidal activity against rice blast and wheat leaf rust. The fungicidal activities of 4-amino-2-quinolinone derivatives of formula(I) according to the present invention prepared by the above examples were tested as follow ; wherein all the test chemicals were readily dispersed in a standard for ulation of acetone in water and a surfactant. Ten ml of acetone containing 10 mg of the chemical was diluted in 90 ml of Tween-20 solution producing 100 ppm solution of chemicals of above examples. Fifty ml of this chemical solution was sprayed to plants on the turntable at the same time. Two pots of plants were duplicately tested for fungicidal activity against 6 plant diseases, respectively. TEST 1 Fungicidal test for rice blast (RCB) Evaluation of activity against blast was done with rice plants in the second leaf stage, grown in 5cm pots with a foliage spray. Fifty ml test material was sprayed on the foliage. After the spray deposit had dried, the plants were inoculated with a suspension of conidia in water (1 x 10 6 spores/ml) and placed in a dew chamber at 25°C for 24 hrs. For inoculum preparation, rice blast fungus was incubated on rice polish agar medium at 26 °C for 2 weeks, and then scratched airial mycelia with rubber and irradiated with near U V light for 2 days. The plants were then held in lighted growth chamber (26 ± 2°C, 85%) for an additional 5 days, and rated on the disease severity. TEST 2 Fungicidal test for rice sheath blast (RSB) Rice plants in the third leaf stage were sprayed with 50ml of chemical solution on the turntable. One day after drying, treated plants were inoculated by injecting inoculum, incubated in wheat bran medium at 25°C for 7 days, macerated into the mixer at the base of the rice plants. The pots were moved to a lighted dew chamber at 28°C and then held for 5 days. The disease severity of each pot was examined and compared with the standard rating diagram. TEST 3 Fungicidal test for cucumber gray mold (CGM) Cucumber plants grown in the first leaf stage were sprayed with 50ml of chemical solution while pots were rotated on the truntable. After the spray deposit had dried for one day, the treated foliage of cucumber was inoculated with conidia (1 x 10 6 spores/ml of B. cineiea), incubated on p_,.__to dextrose agar medium at 25°C for 15 days by leaf spray to all four sides of plants until just before runoff and then placed in 20°C dew chamber for 4 ~ 5 days. The disease rating was made by examining the treated plants and comparing the percent disease on a leaf with the standard rating diagram. TEST 4 Fungicidal test for tomato late blight (TLB) Tests were carried out onto tomato plants grown in 5cm polyvinyl pots for 14 days by leaf spray. The foliage was sprayed to run off with the test chemical while the plant rotated on a turntable. After the spray deposit dried for one day, the treated plants were inoculated by spraying them with a suspension of zoosporangia (1 x 10 5 zoosporangia/ml) incubated on V-8 juice agar medium at 20°C for 2 weeks and then placed in a dew chamber at 18°C for 48 hrs. The disease severity was rated after 4 days of inoculation. TEST 5 Fungicidal test for wheat leaf rust (WLR) Tests were carried out on wheats (cultivar ; Chokwang) grown in polyvinyl pots (diameter ; 5cm) for 7 days by foliage spray. The first leaf was sprayed while plants were rotating on a turntable with 50ml of a chemical solution. After the spray deposit dried, plants were dusted with a uredospores colonied on the second leaf of wheat and placed in a moist chamber at 20°C for 24 hours. One day after inoculation, plant were moved to the plant growth chamber (20 °C , 70% RH) for inducing the disease. The fungicidal effect of the applied chemicals was investigated by observing the share of diseased area after ten days. TEST 6 Fungicidal test for barley powdery mildew (BPM) The barley powdery mildew is an obligately parasitic fungus that must be transferred directly from infected plants to healthy plants in a relatively dry environment. The host plants (cultivar ; Allbori) sowed in polyvinyl pot(diameter ; 5cm) were grown in a greenhouse for 7 days. Healthy young barley with fully expanded primary leaf was sprayed with a suspension of a test material. One day after drying, the applied plants were dusted with conidia of Erysiphe graminis foimed on the primary leaf of barley. The inoculated plants were placed in a plant growth chamber at 22 ~ 24°C and then induced with the powdery mildew. The disease severity was rated after 7 days of inoculation. Fungicidal activity of test chemicals against the above 6 plant diseases is shown in Table 2 calculated by formula below. Percent of disease area in treatment group Control value(%) = 1 - ( | x 100 Percent of disease area in untreated control group Table 2. Fungicidal activity of the 4-amino-2-quinolinone of formula(I) As shown in the Table 2, the compounds of present invention of formula(I) have broad and high fungicidal activity against tested plant diseases, especially, rice blast and wheat leaf rust. Also, the compounds according to the present invention have high insecticidal and miticidal activity against noxious insects, for example, house fly, mosquito, cockroach and agricultral insects, for example, Hemiptera such as small brown plant hopper(Laθ-fep/ιax striatelhis Fallen), brown plant hopper( Nilaparvata lugens Stail), white-backed rice plant ,_opper( Sogatella furcifera Horvath), green rice leaf oτpτpeτ(Nephotettix cinctictps Uhler), greenhouse whitefly( TrialeiLwdes vaporariorum Westwood), and green peach aphid(Myz_.spersicae Sulzer) ; Lepidoptera such as apple lea_mineι{ PΛ V/oπorycter ringoniella Matsumura), diamond- back moth (Plutella xylostella Curtis), rice arm y worm (Pseuclaleti a separata Walker), cabbage __rmyworm(Man7es_ra brassicae Linnaeus), tobacco cut worm (Spodoptera litura Fablicius), and common cabbage worm(P/eris rapae Linnaeus) ; Coleoptera such as rice leaf beetle( Oulema oryzae Kuiwayama), and rice-plant weevil rice curculio(EcΛ-πocπem_.s squameus Billbery). The insecticidal activity of the compounds of the formula(I) according to the present invention was tested by Tests 7 ~ 10 as shown below. The Primary ScreeningO?RI) was designed to detect initial pest control activity of experimental compounds. The types of activity assayed were acute toxicity and growth disruption. The bioassays were designed to detect contact and ingestion activity. The stages tested were as follows : adult brown planthopper(BPH), green peach aphid(GPA), and two-spotted spider mite(TSSM), and 3rd instar diamond-back moth(DBM). All experimental compounds were formulated in 5 ml of acetone c ~ * aining 25mg of 4-amino-2-quinolinone derivatives of formular (I) and diluted with 45ml Triton X-lOO(lOOppm) solution producing 500ppm solution of chemicals of present invention Formulated compounds were applied to the test species with the individual application methods, respectively. TEST 7 Insecticidal test for brown plant hopper (BPH) Root parts of six rice seedlings (cultivar : Dongjin ; 5-6cm in length ; 5-10 day old) were rolled with cotton wool pads and rice seedlings were put into the glass test tubes(φ 3 x 15cm) containing 2ml water. Three to five day-old adult BPH (20 individuals) were collected from rearing cages by an aspirator, and placed into test tubes. Test chemicals were dissolved in 5ml acetone(100%), formulated to the proper concentration in Triton X-100 ( lOOppm), and then sprayed onto the BPH directly. The test tubes were covered with nylon cloth and held in an incubator at 25 °C. Insect mortalities were recorded at 24 and 48 hours after treatment. TEST 8 Insecticidal test for green peach aphid (GPA) Excised tobacco leaf disks (5.5cm in diameter) were dipped into the prepared test chemical solutions (30sec) and taken out. After drying (30min), leaf disks were placed in the petridishes (φ 5.5 x 2cm) and apterous female adult GPAs (20 individuals) were introduced. All petridishes were covered and held in an incubator at 25°C. Insect mortalities were recorded at 24 and 48 hours after treatment. TEST 9 Insecticidal test for two-spotted spider mite(TSSM) Excised kidney bean leaf disks (2.5cm in diameter) were placed on water saturated cotton wool pads fitted into petridishes (φ 5.5 x 2cm). Female adult TSSMs (30 individuals) were placed on leaf disks and prepared test chemicals were sprayed. The petridishes were covered and held in an incubator at 25°C. Mite mortalities were recorded at 24 and 48 hours after treatment. TEST 10 Insecticidal test for diamond-back moth(DBM) Test chemicals were dissolved in 5ml acetone (100%) and formulated to the proper concentration in Triton X- 100 (100 ppm). Excised cabbage leaf disks(5cm in diameter) were dipped into the solution (30sec) and taken out. After drying (30min.), leaf disks were placed in the petridishes (φ 5 x 1cm) and 3rd instar DBM larvae (10 individuals) were introduced. All petridshes were covered and held in an incubator at 25°C. Insect mortalities were recorded at 24 and 48 hours after treatment. The mortality (%) of test chemical against the above insects was calculated by the below formula to list the result as the following Table 3. No. of dead insects Mortality (%) = x 100 No. of treated insects Table 3. Insecticidal effects for 4-amino-2-quinolinone of the formula (I) As shown in Table 3, the compounds of the present invention of formula(I) have good insecticidal activity against diamond back moth(DBM) and miticidal activity against two-spotted spider mite(TSSM). The compounds of formulafl) of present invention have good pre- and post- emergent herbicidal activity against upland and paddy weeds. The herbicidal activity test was conducted according to the following methods. (1) Screening for herbicidal activity in upland condition 5 The sterilized sandy loam soil was mixed with a combined fertilizer and filled in test pots having a surface area of 348cm 2 . After seeding, the pots were covered with the soil finely sieved and kept in a greenhouse at 25 °C mean temperature. Fourteen mg of each compound weighed for 4kg/ha and was dissolved in 7 ml of acetone containing surfactant Tween-20, and diluted with the same amount of water. ι o The solution on soil or foliage applied was in a spray volume of 14 ml/ 348 cm 2 . Test compounds were applied at 1 and 8-12 days after seeding for pre- emergence and post-emergence, respectively. The pots were kept in the greenhouse for 2 or 3 weeks, and the herbicidal activity was visually observed on the basis of morphological and physicological 15 symptoms by percent scale, in which 0 represents no activity and 100 represents complete control. (2) Screening for herbicidal activity in flooded paddy condition. A sandy loam soil mixed with a combined fertilizer and puddled with water to stick mud was filled in test pots having a surface area of 140 cm 2 . 0 Two plant of rice seeding at 3rd leaf stage and sprouted rice seeds were transplanted and seeded, respectively. The pots are watered 3 cm deep just after planting. For 4kg/ha application, 5.6 mg of each compound was dissolved in 2ml of acetone containing 0.2% Tween-20 and diluted with the same amount of water. Four ml of the solution was applied on the water surface of the pot. 5 The pots were kept in the greenhouse for 2 or 3 weeks at 25 °C mean temperature, and the herbicidal activity was visually observed on the basis of morphological and physicological symptoms by percent scale. The plant species employed in these tests were selected from the followings: Test plants for herbicide screening Upland Common. Name Abbreviated Name Scientific Name Paddy Herbicidal activity data of the present test chemical of formula(l) against upland and paddy weeds are shown in Table 4. Table 4. Post-emergent herbicidal activity of the 4-amino-2-quinolinone derivatives (1) (rate = 4 kg/ha). Compound SORBI ECHOR AGRSM DIGSA PANDI SOLNI AESIN ABUTH XANSI CAGHE No. 2 5 8 Table 5. Herbicidal activity of 4-amino-2-quinolinone derivatives (1) to paddy weeds Compound ORYSA ORYSA ECHOR SCPJU MOOVA CYPSE SAGPY No. (3-leaf) (seed) Compound ORYSA ORYSA ECHOR SCPJU MOOVA CYPSE SAGPY No. (3-leaf) (seed) Useful formulations of the compounds of formula(I) can be prepared by mixing the the active ingredients about 0.01 ~ 90 by weight % with proper solid or liquid carrier and supporters such as surfactant, diluent, spreader, synergist, adhesive, and dispersant, etc. The used solid carrier may be chosen from the inorganic powders such as attapulgite clays, the montmorillonite clays, the diatomaceous earths, kaolinite, bentonite, mica, gypsum, calcium carbonate, apatite, synthesized silicone hydroxide hydrate or plant powders. And as liquid carriers, alcohols such as methanol, ethanol, ethylene glycol ; aromatic hydrocarbons such as benzene, xylene, toluene, naphtha; halohydrocarbons such as chloroform, carbon tetrachloride; ethers such as tetrahydrofurane, dioxane; ketones such as acetone, methyl ethyl ketone; esters such as ethyl acetate, butyl acetate, ethylene glycole acetate; amides such as dimethylformamide; nitriles such as acetonitrile; ether alcoholes such as ethylene glycol diethyl ether, or water etc. can b used. Surfactants can be various cationic, anionic and nonionic surfactants. Cationic surfactants include long chain alkylammoniun salts such as cetyltrimethylammonium bromide, etc.. Anionic surfactants include alkali metal, alkaline earth metal and ammoniun salts of alkylaryl sulfonic acids such as dodecyl benzenesulfonic acids; alkylsulfonic acids such as lauryl sulfonic acids ligninsulfonic acid; arylsulfonic such as naphthylenesulfonic acid; lauiyl ether sulfate; fatty alcohol sulfates; fatty acids; salt of sulfated hexadecanols, octadecanols; salts of sulfated fatty alcohol glycol ethers, etc.. Examples of nonionic surfactants include condensation products of fatty alcohols such as oleyl alcohol or cetyl alcohol; phenols; alkylphenols or caster oil with ethylene oxide or propylene oxide; polyoxy ethylene alkylphenylether; poly oxyethylene fatty acid ester, etc.. Polyvinylalcohol, CMC, gum arabic, etc. can be used as adhesive. The compositions of the compounds of the present invention may be manufactured as formulation such as powder, wettable powder, granules, emulsifiable concentrates, suspensions, solution, fumigant, gas phase, etc., and their formulations can be used on earth, agricultural products, seedling, seeds, etc.. For example, emulsifiable concentrates or solution may be prepared by uniformly dissolving the compound of formula(I) with hydrocarbon, acetone or alcohol and surfactant. Wettable powders, which may be compacted to form water dispersible granules, may comprise an intimate mixture of the active compound, inert carrier and surfactants. The combinations including the compounds according to the present invention may be used by mixing with agricultural chemicals such as insecticides, fungicides, herbicides, plant growth regulants, fertilizer, miticides, or other agricultural chemicals. Especially, since the known fungicides have resistance, the compounds of formula(I) of more than 1 weight % may be used with the known fungicides including following compounds ; 1) N-substituted azoles, for example, prochloraz, triademefon, and flusilazol ; 2) pyrimidines, such as fenarimol and nuarimol ; 3) morpholines, such as fenpropimorph and tridemorph ; 4) piperazines, such as triforine ; 5) pyridines, such as pyrifenox ; 6) dithiocarbamates, such as maneb and mancozeb ; 7) phthalimides, such as captafol ; 8) isophthalonitriles, such as chlorothalonil ; 9) dicarboximides, such as iprodione ; 10) benzimidazoles, such as benomyl and carbendazim ; 11) 2-aminopyrimidines, such as ethirimol ; 12) carboxamides, such as carboxin ; and 13) dinitrophenols, such as dinocap. The fungicide combinations of the invention contain at least 1% , generally 20 • 80% by weight of a compound of formula (I).

Claims: WHAT IS CLAIMED IS : A compound of 4-amino-2-quinolinone derivatives of the formula(I) wherein, R j , R 2 , R 3 and R 4 are independently hydrogen, halogen, C ,-C 10 alkyl, C j - haloalkyl, C C g alkoxy, C ,-C 3 haloalkoxy, C j - alkylthio, C j -C 3 haloalkylthio, NO 2 , CN, C ,-C 4 alkoxy carbonyl, phenyl, phenoxy, benzoyl, benzenesulfonyl, benzyl or morpholine ; R s is hydrogen, C j -C 6 alkyl, cyclopropyl, phenyl, halophenyl, benzyl or phenylthiomethyl ; R 6 is selected from hydrogen, C C 5 alkyl, C 3 -C 6 alkenyl and C 3 -C 6 alkynyl group; R 7 is wherein, R g , R 9 , R, 0 , R n , R, 2 , R 13 , R 14 , R 15 , R I6 is hydrogen, halogen, C,-C 6 alkyl, alkoxyalkyl, halophenyl, phenyl or ( ^Si and R 8 , R 9 , R 10 are not hydrogen at the same time ; R 17 is hydrogen or C,-C 5 alkyl ; R lg , R 19 is C,-C 5 alkyl ; X is oxygen or sulfur ; Y is sulfur or -S(=O)- ; R JO is -G- alkyl ; 5 m, n, p, q is 0 to 4 . 2. The compound of 4-amino-2-quinolinone derivatives (I) according to claim 1 wherein, R,, R 2 , R 3 and R 4 are independently hydrogen, halogen, C ,-C 6 alkyl, CF 3 , NO 2 , ι o CN ; R 5 is hydrogen, C,-C 4 alkyl, cyclopropyl, , halophenyl, benzyl ; R 6 is selected from hydrogen, C r C 5 alkyl, C 3 -C 6 alkenyl and C 3 -C 6 alkynyl group; R- is _ (CH 2 ) p -γ- R 19 , — CH 2 CN , - ■ wherein, R g , R 9 , R 10 , R„, R 12 , R 13 , R 14 , R 15 , R 16 is hydrogen, halogen, C r C 6 alkyl, 0 alkoxyalkyl, phenyl or (R-^Si and R 8 , R 9 , R 10 are not hydrogen at the same time ; R 17 is hydrogen or C ] -C 5 alkyl ; Ru, R 19 is C.-C 5 alkyl ; X is oxygen or sulfur ; 5 Y is sulfur or -S(=O)- ; R 20 is C.-C 5 alkyl ; m, n, p, q is 0 to 4 3. The compounds of claim 1 which are described in detail in the Table 1. 4. Fungicides including a fungicidal effective amount of 4-amino-2-quinolinone derivatives having the formula (I) as an effective ingredient. 5. Insecticides including an insecticidal effective amount of 4-amino-2-quinolinone derivatives having the formula (I) as an effective ingredient. 6. Herbicides including a herbicidal effective amount of 4-amino-2-quinolinone derivatives having the formula (I) as an effective ingredient. 7. A process for preparing the compounds of 4-amino-2-quinolinone derivatives of formula (I) by reacting the 4-sulfoxy-2-quinolinone derivatives of formula (II) with amine derivatives(III) or amine.acid salts(IV) in an inert organic solvent wherein, R R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are defined as described above in claim 1 and HX represents organic or inorganic acids .

Inventors: CHOI EUN BOK, CHOI GYUNG JA, LEE GE HYEONG, LEE HYEON KYU, LEE JIN PYO, PAK CHWANG SIEK, YANG HEUI CHEOL, YON GYU HWAN, CHOI, EUN, BOK, CHOI, GYUNG, JA, LEE, GE, HYEONG, LEE, HYEON, KYU, LEE, JIN, PYO, PAK, CHWANG, SIEK, YANG, HEUI, CHEOL, YON, GYU, HWAN
Applicants: CHOI EUN BOK, CHOI GYUNG JA, KOREA RES INST CHEM TECH, LEE GE HYEONG, LEE HYEON KYU, LEE JIN PYO, PAK CHWANG SIEK, YANG HEUI CHEOL, YON GYU HWAN, CHOI, EUN, BOK, CHOI, GYUNG, JA, KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY, LEE, GE, HYEONG, LEE, HYEON, KYU, LEE, JIN, PYO, PAK, CHWANG, SIEK, YANG, HEUI, CHEOL, YON, GYU, HWAN
Application year: 1994
Main classification: C07D215
IPC codes: A01N43, A01N55, C07D215, C07D221, C07D401, C07D405, C07D409, C07D491, C07F7